Water → HCID 135677574, compound

HRID 1974346Notes

Reaction equation

HRID 1974346 reaction equation
Cl[C:2]1[C:10]2[NH:9][C:8]([CH:11]([F:13])[F:12])=[N:7][C:6]=2[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].C(N(CC)CC)C.[C:27]([NH2:31])([CH3:30])([CH3:29])[CH3:28].O>C(O)C>[C:27]([NH:31][C:2]1[C:10]2[NH:9][C:8]([CH:11]([F:13])[F:12])=[N:7][C:6]=2[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 1356775854-Chloro-2-(difluoromethyl)-5,7-dinitro-1H-benzimidazole

Product 1

HCID 135677574HCID 135677574, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloro-5,7-dinitro-2-difluoromethylbenzimidazole (1.9 grams), triethylamine (0.7 gram), and tert-butylamine (0.5 gram) were mixed in ethanol and refluxed overnight. The mixture was then poured into water, acidified, and filtered to separate the expected 4-tert-butylamino-5,7-dinitro-2-difluoromethylbenzimidazole product, m.p., 189°-196° C. After recrystallization from ethanol, it melted at 199°-201° C. The identity of the product was confirmed by NMR analysis.

Workup

  1. temperaturerefluxed overnight
  2. filtrationfiltered
  3. customto separate the expected 4-tert-butylamino-5,7-dinitro-2-difluoromethylbenzimidazole product
  4. customm.p., 189°-196° C
  5. customAfter recrystallization from ethanol, it melted at 199°-201° C

Sources & evidence

ORD record
ord-c0841e95badc48d38fd57fd926d3ef74
Source dataset
uspto-grants-1976_12
Patent number
US04000295

Reaction notes

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